How to Pick the Right Startup to Join

Not all startups are created equal

So you want to join a startup. You’re excited about the growth opportunities, the chance to work on something high impact, and the fast-moving culture. But not all startups are created equal. Joining a great startup can be an inflection point in accelerating your career. Joining a bad startup can lead to burnout, frustration, and disenchantment. With so much on the line, how do you pick the right one?

I’ve experienced a spectrum of startups — from a 3-person startup that I co-founded to a mid-stage 30-person startup. In my latest job hunt, I reflected on my own experiences as well as the experiences of friends in the space. I consulted many people wiser than me. Through this process, I came to the conclusion that there are are 3 important questions to ask when evaluating a startup: Would I invest in the company? Will I be working with smart and supportive people? And does the company approach growth thoughtfully?

Would you invest in the company?

By working for a company, you are essentially investing in them. There is an opportunity cost to joining any particular startup. You could be working for another startup, working for a more established company with less risk, or doing something else altogether. It’s important to evaluate the potential employer with an investor’s lens. Are you willing to put your personal savings into this startup?

From a pragmatic perspective, you want to ensure that you have job security. You also want to maximize your payoff — both in terms of the value of your stocks as well as the company’s future brand value on your resume. Working for an investable startup has the added benefit of doing work that is valuable and meaningful. Your impact is more likely to be long-lasting.

There are two key questions that can help you think about whether you would invest in a company:

1. Does the product make sense? Do you think what the company builds is valuable for the world? Or do you think it’s gimmicky and over-hyped? This is the easiest to evaluate if you are a potential user of the product. But if you are not, try to find someone that is a potential user or has knowledge of the industry and ask them what they think of the product.
2. Do you believe in the leadership team? Are you confident that the right people are in charge? Are they people of character? Are they persistent? Are they transparent and approachable? If available, read their published blog posts, or watch their recorded interviews to get a glimpse into how they think. It may also help to ask current employees what they think of their leaders.

Will you be working with smart and supportive people?

Once you’ve determined that the company is headed in the right direction and has the right people at the helm, you should look at who is currently working there. In my experience, I learn the most when I surround myself with smart people who are willing to share their knowledge and help me grow. Moreover, a team of smart people will increase the startup’s chances of success, which leads back to my first point of working for an investment-worthy startup.

The best way to answer the question of “Will you be working with smart and supportive people?” is to meet as many people at the company as possible. If you are extended an offer, ask your recruiter or hiring manager to set you up with video calls, lunches, and coffee chats with both managers and peers.

During these interactions, ask questions like:

• What did you do before this?
• What did you have to give up to be here? Did you have to quit a good job? Move cities? Take a pay cut?
• What interesting problems have you solved lately?

After these conversations, think about:

• Do I feel comfortable with this person?
• Does this person strike me as intelligent and ambitious?
• Does this person speak about their work with passion?

Does the company approach growth thoughtfully?

When I was hunting for a job, I saw it as a red flag when a recruiter says something like, “We are doubling our engineering team in the next 6 months.” without telling me how they were managing this growth carefully. An expanding team has the potential to lead to many problems such as ambiguous responsibilities, ineffective communications, and politics. Companies can also fall into the trap of over-hiring and later move employees to jobs outside their interest or worse, lay them off. When evaluating a startup that has ambitious growth plans, it is important to ask:

• What is the growth projection for the team? How were these numbers calculated? Are they based on real needs, or are they based on a vague idea of a “good size” for the company?
• What does the company do to ensure there’s adequate mentorship and on-boarding for new employees?
• What is the junior to senior employee ratio? What is the manager to direct reports ratio? (Generally anything above 10 direct reports per manager is too high, unless it is for a seasoned manager that spends almost all of their time doing management.)
• How has the company adapted its internal communication channels and strategies as the team has grown?
• What “growing pains” has the company experienced already? How has it addressed them?

The Takeaway

Thinking about how investment-worthy a startup is, whether it is filled with smart people, and whether it grows carefully will help you determine if it is an organization worth your time and commitment. However, this is not an exhaustive list and you may have additional criteria depending on your work style and values. For example, you may also want to consider factors such as salary, benefits, hours, mission, and whether the team is remote-work friendly.

Another thing to note is that the growth and learning opportunities found in a startup can sometimes also be found in bigger companies within certain teams. In my current role as a Software Engineer on the Firebase team at Google, I experience a high degree of impact, challenge, and ownership due to the team’s startup roots. (It was acquired by Google.)

Joining a startup has high risks and high returns. Spending extra time and effort during your job hunt to ensure that you are joining the right startup is a worthwhile investment that will pay off. Who knows, you may get lucky and join the next unicorn company.

Photo by Clem Onojeghuo on Unsplash

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